


riding riley

by poetictragedy



Category: Supernatural
Genre: Dirty Talk, Dry Humping, Fingerfucking, First Time, Frottage, M/M, Masturbation, Plushophilia, References to Underage Drinking, Sibling Incest, Underage Sex, Verbal Humiliation
Language: English
Status: Completed
Published: 2013-06-24
Updated: 2013-06-24
Packaged: 2017-12-16 00:23:43
Rating: Explicit
Warnings: Underage
Chapters: 2
Words: 5,219
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/855670
Author URL: https://archiveofourown.org/users/poetictragedy/pseuds/poetictragedy
Summary: <blockquote class="userstuff">
              <p>Dean catches 12 year old Sam having some... <em>fun</em> with his teddy bear and joins in.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Written for the [spnkink-meme](http://spnkink-meme.livejournal.com/) and this prompt: _Dean catches Sammy (12) naked humping his big teddy bear. Dean joins Sam on the bed and make him come humping his stuffed bear. Dean just push his dick out his pants and rub it against Sammy's tiny ass until he comes over it. No "baby boy" talk please. First time weecest. Dean talks dirty to Sam,encourage him to hump it harder, almost humiliate him. Sammy gets off of it though._
> 
> And, yes, Sam is 12 and Dean is 16. So if that's not your cup of tea that's fine and great but please do not comment and bash this. I'm merely writing something and it's totally fictional, etc, etc.
> 
> I apologize for any mistakes you find.

It’s been nearly an hour since Sam stomped up the stairs and holed himself up in his bedroom. He hasn’t come down, not even once, and Dean hasn’t heard a peep out of him since he slammed the door shut behind him.  
  
And Dean would be lying if he said he wasn’t worried. He hasn’t seen Sam in a mood like this, one where he doesn’t want to talk to anyone and where he’d rather be alone in his room.  
  
For sixty minutes, the eldest brother doesn’t move from his spot on the couch and he doesn’t call out to his brother, fearful of pissing Sam off any more than he already is.  
  
Soon, though, it starts to eat away at Dean and he gets up, flicking the television off before throwing the remote down on the couch. He moves up the stairs, his boot-clad feet stomping against the old wood, and when he gets to the top of the stairs, Dean listens for any noise.  
  
Nothing; Sam’s as quiet as a fucking mouse.  
  
Dean sighs and runs a hand down his face, dropping it as he walks down the hall, stopping in front of his brother’s room. He presses one ear to the door, wraps his hand around the knob, and frowns when he hears the bed springs squeaking.  
  
The door opens and the hinges squeak, though not as loudly as the mattress springs, and what Dean sees in the room has his breath catching in his throat.  
  
Because there’s Sam on his bed, naked as the day he was born, with a giant teddy bear underneath him. He’s humping the damn thing, so preoccupied in his actions that he doesn’t notice Dean standing there; not until the teenager inhales sharply.  
  
Sam’s head snaps toward the door and his eyes go wide. “Dean,” he breathes, his cheeks turning red as he pulls away from the bear.   
  
“What are you doin’, Sammy?” It’s all Dean can think of to ask, his mind too blown and too jumbled with other thoughts to come up with something better.  
  
“Um…”  
  
That one word hangs in the air and soon Dean’s snapped out of his reverie, dragging his tongue across his lips as he shuts the door. Sam’s still looking at him like a deer caught in the headlights and the teen allows himself to look at his brother — whose cock is hard between his legs.  
  
It’s not the first time Dean has walked in on Sam with a boner and he knows that it’s certainly not the last, but this?  _This_  is the weirdest thing he’s ever seen before and in the world they live in, that’s kind of hard to say.  
  
“Are you mad?” Sam’s voice is squeaky and high pitched, in that awkward stage between child and “man”, and Dean shakes his head, eyes locked on his brother’s body. “Don’t tell dad.”  
  
Dean laughs and shakes his head. “I’m not telling dad.”  
  
“Wh - why not?”  
  
“Sam, you were fucking a teddy bear. You really think that’s something dad needs to hear about?” Sam makes a face, like he’s considering this, and shakes his head as Dean comes forward. “Keep going,” he whispers.

The kid blinks and looks between Dean and the bear. “You want me to ke - keep going?”  
  
“If Riley doesn’t mind.” The teddy bear, who Sam named Riley three years ago, lies face-first on the bed with his ass in the air. There’s a damp spot on his back and Dean groans, letting his eyes flutter shut for a second. “I can’t believe you were fucking a teddy, Sam,” he whispers.  
  
Sam makes a noise and grabs the bear again, scrambling onto his knees once more. He presses his hips against the bear’s ass and starts to hump the damn thing once more, whimpering quietly. The noise goes straight to Dean’s cock and he knows he should be disgusted — both from getting hard because it’s Sam and because his bother is fucking a toy.  
  
Though he isn’t disgusted, Dean pretends he is; just to see what reaction he’ll get from Sam.  
  
“Look at you,” he murmurs, moving back so he’s sitting near the end of the bed where he has a better view. His cock is getting harder, pressing against the front of his jeans, but Dean ignores it. “Fucking that bear like such an eager little slut. Is that what you are, Sammy, a slut? A slut for that teddy..”  
  
Sam moans and leans over, his body pressing against the bear’s.  
  
A hum settles in Dean’s throat and he licks his lips. “Yeah, Sammy, fuck that filthy little bear. You wish he was someone else, huh?” When his brother nods and moans, Dean grins. “You gonna tell me who?”  
  
“N - no,” Sam answers.  
  
“Alright, keep fucking your dirty little toy. You do this often?” Sam nods his head, his cheeks and neck turning a bright pink. “ _Shit_ , Sam. You’re fucking dirty, you know that? I don’t know anyone who fucks a big bear like this, especially not little boys like you..”  
  
Sam pants and the springs squeak louder than before. He’s got a hand gripping the bear’s shoulder, the other wedged between the stuffed animal and the mattress as he ruts against him harder.  
  
“Yeah, that’s it,” Dean purrs, moving to take his shirt off before throwing it onto the floor, dropping his hands down to undo his jeans. “Fuck Riley with your little cock even harder.”  
  
“D - Dean.”  
  
“Yeah?”   
  
No response comes for a few minutes; Sam just pants and keeps rutting against the teddy bear underneath him. He gasps and turns his head, eyes fluttering open to look at Dean, who stares back at him, eyebrows raised expectantly.  
  
Sam licks his lips and closes his eyes. “I’m gonna…”  
  
“Gonna what?” Dean asks and chuckles before Sam can reply, leaning in close so he can whisper, “You gonna come all of your teddy, Sam? I bet you’ve done that so many times, got Riley so fucking filthy. God, that’s so fucking weird, Sam, but so incredibly hot.”  
  
“Dean…”  
  
“How long have you been doing this?”

A whimper escapes Sam’s throat before he says, “T - two years.”  
  
The admission makes Dean swallow at the lump in his throat and he shakes his head, running a hand over Riley’s furry head. “Come on, Sam, I know you can fuck him harder… or do I have to show you how to fuck?”  
  
Dean knows that Sam’s only twelve, that he hasn’t had any experience, and all he knows about sex he gets from school and the occasional porn either John or Dean watch. He also knows that he’s being hard on his brother but he wants to see how hard he can fuck, wants to see him do it in earnest.   
  
It takes Sam a few more minutes (which tells Dean he’s been up in his room fucking the bear for a while) but he eventually comes. He gasps and grunts, little hips digging into the furry ass of the teddy, and Dean has to grip his cock through his jeans and underwear to keep himself from coming on the spot.  
  
“God damn, Sammy.” Dean whistles and shakes his head, grinning as he stands up to get his jeans and boxers down just past his ass.  
  
Sam looks over his shoulder and whimpers. “What - what’re you doing?”  
  
Instead of answer, Dean spreads Sam’s ass and rubs the head of his cock against the kid’s hole, running it around the rim. He moves one hand away and wraps it around the base of his shaft, stroking himself quickly as he listens to Sam pant harshly.

The replay of what happened plays through Dean’s mind and he continues to rock his hips forward, moving his cock along the crease of Sam’s ass. When he gets closer to coming, he throws his head back and moans loudly, hips stuttering forward as he grunts.  
  
“Sam,” Dean moans, dragging his brother’s name out as he comes all over the kid’s ass and lower back. He breathes hard, coming down from his orgasm quickly, and falls onto the mattress with a huff. “Damn.”  
  
The two of them breath harshly together before Dean eventually stands, doing his jeans up before bending down to grab his shoes and shirt. He walks over to the bedroom door, opens it, and stops in the doorway.  
  
“Tell me when you fuck Riley again,” he says and grins when Sam gasps, his eyes focused on his big brother. “I want to get my cock in you while you rub up against him.”  
Sam moans and closes his eyes, causing Dean to chuckle as he walks down the hallway. He leaves his younger brother to clean up both of their messes and goes back downstairs to watch television.  
  
When Sam comes back down fifteen minutes later, they both act like nothing happened.


	2. Chapter 2

**Summary for the Chapter:**

> Dean _finally_ gets to fuck Sam.

**Notes for the Chapter:**

> The conclusion of "Riding Riley." As requested by several people. :)
> 
> I apologize for any mistakes you find, like always.

Weeks pass before they’re alone again.

-

Jobs are few and far between now a days, which forces John to take the boys over to Bobby’s house for a while. He works odd jobs with the other hunter, both of them fixing the occasional car for neighbors and people they meet at the grocery store.

But salvation comes in the form of a poltergeist and Dean’s never been happier to hear about a malevolent spirit in his entire life. He keeps his emotions in check, though, when John tells him he’s taking Bobby along for the ride and when he says they’ll be gone for a week, Dean nearly bursts with happiness.

For the past three weeks, Dean and Sam have had little to no privacy in the house, not even late at night in their room. If John and Bobby aren’t hanging around, it’s one of the neighbor women bringing them pies or casseroles as an excuse to wait for the older men.

And the lack of private time has taken it’s toll on both of them.

Dean can see the way Sam fidgets whenever he looks at Riley and seeing him look at the damn bear with lust in his eyes only makes Dean anxious. He gets hard several times just watching Sam cuddle the stuffed animal and has to excuse himself from the room to get a grip on himself.

Now, though, they’ll be alone for a glorious five-to-seven days, depending on the severity of the situation, and Dean’s body is thrumming as he helps Bobby and John load their things into the truck.

“Watch out for your little brother,” John says and grins at Dean.

“Yes sir.” 

Bobby claps a hand on his shoulder, giving him a stern look. “Don’t break anything in my house, ya hear?” he asks and Dean laughs, nodding as he promises to take care of Sammy and to not break anything in the house.

With one final goodbye to both boys, John and Bobby hop into the truck, the engine roaring to life a moment later. The black GMC Sierra pulls away from the house, gravel crunching underneath the tires.

Dean waits until the truck is long gone before going back inside. Sam is right on his heels and he runs up the stairs, no doubt going to their bedroom to have some alone time with Riley. Which is fine with Dean; he wants to raid the fridge, anyway, and figures he can let Sam come  _once_  before going up to fuck him.

And that’s what Dean has been waiting for: the day he can finally fuck his little brother. He’s been gathering supplies whenever he goes to town alone, stashing condoms and lube into his duffel bag when everyone is asleep.

The thought of his cock sliding into Sam makes Dean’s cock harden in his jeans and he cups himself through the denim, squeezing.  _Not yet_ , he thinks as he makes his way to the fridge, opening the door quickly. Beer bottles line the second shelf and he grabs one, twisting the top off as he heads back to the stairs.

Dean takes his sweet time, picturing what Sam’s doing as he walks. He thinks about his younger brother taking his clothes off, scrambling to get them off so he can mount Riley, who is undoubtedly laying on the mattress with his furry ass in the air.

“Shit,” he mumbles, swallowing hard. He takes a long pull from the bottle, licks his lips, and stops at the top of the staircase. The house is quiet and then…

Yep. The mattress is squeaking already. Damn, Sammy is a quick and eager little thing, isn’t he? Dean smirks and walks to their bedroom, where the door is pushed wide open, and leans against the frame.

Sam’s already on the bed but this time instead of having Riley face down, he has the teddy bear on it’s back. Dean nearly chokes on a mouthful of beer at the sight, coughing quietly. The noise catches his little brother’s attention and Sam looks up, cheeks reddening.

“I’m fine,” Dean says, waving a hand with a smile, “and you can continue.”

“Okay.” As he speaks, Sam looks down at Riley and puts his hands on either side of the bear’s head, rocking his hips forward. He mewls and pants at the friction, the noises going straight to Dean’s cock, and he watches with his mouth open, the bottle of beer halfway to his lips.

 _That is too hot_ , Dean thinks, and he downs the rest of his beer before coming into the room, setting the empty bottle on the nightstand. Sam ignores him, too focused on the bear underneath him, and he snaps his hips forward.

Once the beer bottle is abandoned, Dean undoes his jeans. He’s already barefoot, has been since he got back from the store with Bobby earlier, and slips the denim off easily. It falls to a heap on the floor and he takes his shirt off, throwing it somewhere into the corner.

Sam makes a whimpering noise and Dean smirks, turning to see his younger brother’s gaze on him. His eyes turn away and settle on the bear’s face when Dean catches him, though, his neck and face turning pink.

“Aw, Sammy,” Dean murmurs, laughing. “You don’t have anything to be shy about. I’ve seen you fuck that teddy bear before and you’ve seen me naked a thousand times.”

Still, it’s pretty cute that the kid is embarrassed. Maybe he remembers what Dean said before, about fucking him while he fucks the bear, and the thought makes the teenager shudder. He sucks in a deep breath and goes over to the corner where he keeps his duffel, bending down to rummage through it.

Dean brings out a box of condoms and a small bottle of lube. He actually stole the lube from the drug store, slipping it into his pocket while he flirted causally with the young girl behind the counter. The condoms? Well… he had to pay for those, unfortunately, because the box was too big to get into his jacket pocket.

When he turns around, Sam is fucking Riley in earnest. He’s making noises that only make Dean’s cock throb against the front of his boxers and he grips himself, biting his lower lip.

“Looks like you’re having fun,” he murmurs, coming over to sit on the edge of the bed, running a hand along the middle of Sam’s back. “I bet you’re getting ready to come, aren’t you?”

Sam nods his head and drops down, pressing his body against Riley’s, his hips snapping forward. He curls his hands around the bear’s ears and breathes hard, moaning as his entire body shudders. Dean watches him come undone and closes his eyes briefly, taking a deep breath.

Several minutes pass and Dean stands, getting out of his underwear because he hates feeling confined. Besides, the strain of the cotton only made his cock hurt more than it already was. He kicks the fabric away and watches Sam roll off Riley, his cock red and wet.

“Damn.” Whistling, Dean shakes his head and grabs the bottle of lube, deciding that it’s now or never. He knows Sam will get hard quickly, thanking every god and archangel he knows the names of for quick refractory periods.

The boy on the mattress opens his eyes and looks up at Dean. “Are you gonna — ?”

He doesn’t even need to finish the question; Dean knows what he’s asking and nods his head. Sam shivers and closes his eyes, tongue darting out across his lips as he spreads his legs. 

And, god, Dean knows he’s going to hell for finding his baby brother attractive but oh fucking well. Sam’s tall for his age, lean in all the right ways with some muscle here and there, and his cock is bigger than a normal twelve year old’s — or so Dean is guessing.

Riley gets pushed to the side and Sam moves around under Dean’s command, laying along the middle of the bed. He’s got his legs spread as far as they can go, knobby knees bent, and feet pressed against the mattress. His body is trembling, Dean can see that clearly now, and the thought that _maybe_  they shouldn’t do this crosses his mind.

Before he can turn around and stop, though, Sam lifts his hips. “I’m ready,” he says, simply, his voice a tad breathless and his cheeks flushed.

“God damn.” Shaking his head, Dean pops the top on the lube and settles onto his knees in front of Sam, sitting back on his heels. He pours some of the lube (the warming kind) onto his fingers and drops the bottle onto the mattress by his leg.

Then slowly, ever so _fucking_ slowly, he presses a finger against his brother’s hole, running the tip along his rim teasingly. The noise that leaves Sam’s throat makes Dean’s cock throb and ache and he wants to be inside of him  _now_  — but has to wait, he knows.

Because hurting Sam is the  _last thing_  Dean wants to do.

“Push it _in_.” 

“Bossy little shit,” Dean murmurs and smacks Sam’s thigh playfully. It’s just barely a tap, nothing they haven’t done before, but the boy lets out a whimper. That noise makes the teenager’s heart ache and he rubs his hand along Sam’s leg, thumb brushing slow circles along the smooth, pale flesh.

When Sam seems to be okay, if not more than a little eager, Dean lets the tip of his finger breach the boy’s rim. He pauses, holding his breath as he looks up at the sweet face of his baby brother and when he sees no signs of distress, keeps moving his finger in little bit little.

“Ow.” Sam hisses the word when Dean’s finger is halfway into him and he wiggles his hips around, whimpering. “Hurts,” he says.

Dean swallows and leans up, kissing Sam’s stomach. “I know,” he murmurs, his free hand running along his brother’s leg soothingly. “But just relax for me and it’ll stop hurting, okay? I promise.”

Sam’s still a little hesitant, so the teenager says, “Have I ever let you get hurt before?”

“No…”

“See? And I’m not going to let it happen again. Now  _relax_.”

The words seem to calm the younger Winchester down because he takes a deep breath and lets his eyes flutter shut. His muscles loosen around Dean’s finger and he slips it in all the way, only having to stop one or two times when Sam makes an uncomfortable noise.

“How you feeling, Sammy?” Dean asks, his voice soft.

“G — good.” A deeper shade of crimson floods in Sam’s cheeks as he starts to move his hips slowly, pressing back against Dean’s hand. He gasps sharply and, at first, Dean thinks he’s in pain but the noise tapers off into a moan.

A delicious, porn-star worthy moan. Well…  _amateur_  porn star, anyway.

Dean, feeling encouraged by those noises, starts to pump his finger in and out slowly, getting Sam used to the feeling of just one. His muscles are almost completely lax by this point, though they tighten up whenever the digit tries to push back in, but a few soft words from Dean has Sam opening right up.

“You’re doing  _so good_ ,” the teenager murmurs, bringing his finger out before pressing a second one against Sam’s hole. “Such a little slut for this, huh? First for Riley and now for me..”

“Yeah,” Sam moans, his chest rising and falling heavily with each harsh breath. His back bows off the bed when Dean gets two fingers into him, slipping them in quicker than before, and he twists the sheets in his hands.

Dean stills his hand, waits for Sam’s okay, and starts to open him up a little more, wanting to get it over with quickly. There’s no way he can last long with Sam moaning and writhing and gasping just from his fingers alone. God, he already wants to jerk off and come all over the boy. 

But, no — he has to  _wait_  to fuck him. That is what he promised, right?

The two digits slip in and out easily after a few minutes. When Sam starts begging for more, saying things Dean is shocked to hear come out of that mouth, the teenager slips a third finger in.

It’s tricky, Dean finds, and he has to pour more lube onto his fingers before pushing them into Sam, separating them slightly. That causes the boy to hiss and to kick a leg out, probably trying to kick Dean, but the teenager catches it.

“Don’t move,” he says, a warning in his tone. 

Sam nods meekly and tips his head back, pushing his hips back against Dean’s hand, gasping his name sharply. This is something he’s never done to himself and up until a few weeks ago, hadn’t really processed or thought about at all.

Yes, Sam has had the occasional wet dream about Dean — but it was never like  _this_ ; the boy simply dreamed about his brother kissing him or touching his cock. 

It seems like it’s been forever but Sam is finally loose enough for Dean to fuck him without hurting the boy too much. He slips his fingers out, grabs the box of condoms and pulls one out, putting the package between his teeth.

The box gets thrown over the edge of the mattress as Dean straightens up, looking down at the boy in front of him. He’s trying to figure out a way that he can fuck Sam and still allow the boy to grind against his teddy bear.

“On your knees,” he says, suddenly, the foil packet falling from between his lips and landing on the mattress. Sam looks dazed, his green eyes dark and pupils blown, but nods and scrambles onto his knees.

Dean picks Riley up then, flips him over onto his stomach, and shoves him under Sam’s body, making sure his ass — and the furry tail — are pressed right against his brother’s cock. 

Once that’s done, the teen picks the condom up and rips the top off, taking the latex out of the foil. He knows that he’s clean but doesn’t want to risk anything since this is Sam’s first time and all. Plus, they can ditch the condoms after Dean gets tested again.

“Just relax.” The words come out soft and Dean smiles, looking up at Sam after he’s gotten to condom rolled down over his cock. The boy’s got his body leaned over against Riley, his ass high in the air, and arms folded on the back of the bear’s head.

And, god, that sight is inviting and beyond hot. Next time, Dean thinks, he’s going to rim Sam and maybe even blow him. One thing at a time, though, because he doesn’t want to overwhelm the boy with too many things at once.

Picking the bottle up, Dean pours some onto his palm and strokes it over his cock slowly, biting down on his lower lip. He’s been neglecting his hard on for a while now, since he walked in on Sam fucking the toy, and the movement hurts and feels good all at the same time.

Without wasting anymore time, he throws the bottle down onto the bed and comes forward, wrapping one hand around the base of his cock. It seems surreal to Dean that he’s about to fuck Sam, who will undoubtedly be hotter and tighter than anything else he’s ever fucked.

“Shit.” Dean laughs and smooths his fingers along the boy’s skin when he asks if everything’s okay. To which Dean replies with ‘ _yeah, everything is fine, Sammy_ ’ before pressing the head of his cock against Sam’s entrance.

The head slips into Sam and they moan in unison, though the boy’s is higher and more pained than Dean’s. He soothes his baby brother with soft touches and words, leaning over to kiss his shoulders. 

When Sam’s ready for more, Dean slips another inch into him; then another… and another… and finally another until his entire length is buried into the boy. God, he’s so tight that Dean actually thinks he may come in less time than he normal does and won’t that be embarrassing?

“Fuck against Riley while I fuck you,” he instructs, just barely moving his hips against Sam, going slow until the whimpers and moans stop sounding sharp and hurt.

And that takes another five minutes. 

Five long minutes of Dean just rocking into Sam, his hands wrapped around the boy’s skinny hips, nails digging into his skin. He starts to thrust in and out when Sam tells him that there’s no more pain, just a dull ache that he can handle.

Hunters, Dean thinks as he slams into Sam for the first time, can handle any kind of pain there is and his baby brother’s doing a good job. He’ll be a great hunter and an even better lay, if that’s something he wants from Dean after this, of course.

“Dean…” Sam’s whine pulls the eldest out of his reverie. “Fuck,” he says and squeaks, no doubt blushing because he said a bad word.

“S’okay.” A laugh bubbles up from Dean’s throat, tapering off into a moan as he starts to rock harder against Sam. The push-pull of it all and the way Sam’s hips move against his own as he fucks Riley make Dean’s head spin.

It’s never been this good and Dean knows that it never will be. Not even if he fucks a hundred different girls; Sam will always —  _always_  — be his favourite.

Dean’s hands wrap around Sam’s hips tighter and he pulls him back against his cock, slamming it in quickly. A sharp, pained cry fills the air and the teenager stops, moving a hand up to run through Sam’s hair.

“You okay?” A weak nod; a whimper. “Sammy…”

“I’m  _fine_ ,” Sam snaps, his voice breathless. “Just… hurt.”

Frowning, Dean nods and kisses the back of Sam’s head before pulling back, slipping one hand underneath both the boy and his bear. He pushes Riley up against Sam’s cock, his body pushing the smaller boy down against the bear, fucking into him slowly.

“Dean..”

“Mmm?”

“Gonna..” Sam’s words are cut off by a moan and he buries his face against the back of Riley’s head, moving his little hips as hard and fast as he can. 

A smile spreads across Dean’s face as he leans down to whisper against his brother’s ear, “Come for me. Come all over Riley’s ass while I come in yours. You want that, don’t you?”

“Yes.” The word is muffled but Dean catches it anyway.

“Then fucking come.” The teenager punctuates the words with a sharp thrust of his hips, the hand underneath Riley pushing him against Sam even more. He continues to fuck his brother, breath falling hot and wet against his ear, and whispers dirty things.

Things about Sam being a cock slut and wanting Dean to fuck him while he rides against the toy he’s had since he was nine. Fucking  _nine_ , he says, gasping the word as he slams in one more time, dragging his cock out halfway before snapping his hips forward.

And Sam comes just like that. He writhes and moans, his hands curling around the brown fur of the bear underneath him. The movements of his hips become erratic before they stop completely and Sam’s body goes limp, all the breath rushing out of his lungs at once.

When he comes, Sam’s muscles tighten around Dean and it's so fucking perfect and amazing that he nearly blows his load right there but somehow manages to hold off. He praises Sam then, tells him how good he was and how amazing he feels and how badly Dean wants to come inside of him.

“Come… in me,” Sam croaks.

Dean groans, his head falling between his shoulder and resting against the other’s, breath coming out in harsh pants. He continues to fuck Sam, sliding his cock in and out of that perfect, tight heat for another minute before his orgasm hits him like a punch.

Air catches in his throat for a second and Dean moans loudly, his hips pressed against Sam’s ass as he experiences  _the best_  orgasm of his life. Not even Mary Beth from three jobs ago in Kentucky could have given him a better orgasm and she had the mouth for sucking cock — and the skill.

When he comes down from his orgasm, Dean falls on top of Sam for a moment and just breathes, taking everything in. The room smells like sex and sweat and Dean grins lazily, knowing that if they do this often they’re going to have to spray air freshener around before Bobby and John come back.

“That was fucking awesome,” the teen murmurs, kissing the side of Sam’s head before pulling out, hissing. The boy underneath him hisses too and rolls over, his cock redder than before. Dean frowns, says something about getting him some lotion for it later, and tells him to limit his fuck sessions with Riley before he rubs his dick raw.

And Sam laughs, swatting playfully at Dean. “Gonna nap now,” he says, yawning loudly as he turns Riley over, hugging him chest-to-chest.

The fact that Sam can go to sleep with the bear after fucking and coming all over him blows Dean’s mind. It also turns him on, too, but he’s too spent to think too much about it, just shrugs it off and pushes the image into his wank bank for later.

Dean cleans up, throwing away the condom and the wrapper and stashes the lube and condoms back into the bag just in case their dad and Bobby come back for god knows what. After that’s done, he sprays some kind of fruity, berry air freshener around the room, nearly choking on it as he walks around.

And, once that’s done, finally climbs into bed with Sam. He lays behind his brother, arm looped around his tiny waist, and his hand resting on Riley’s back. For the first time having sex, Dean thinks Sam did amazing and knows there’s a lot more he could teach him…

But, for now, he just falls asleep with Sam and Riley in his arms, not thinking about the fact that he’s in a threesome with his underage brother and a goddamn teddy bear.


End file.
